Retene
Chemical compound From Wikipedia, the free encyclopedia
Retene, methyl isopropyl phenanthrene or 1-methyl-7-isopropyl phenanthrene, C18H18, is a polycyclic aromatic hydrocarbon present in the coal tar fraction, boiling above 360 °C. It occurs naturally in the tars obtained by the distillation of resinous woods. It crystallizes in large plates, which melt at 98.5 °C and boil at 390 °C. It is readily soluble in warm ether and in hot glacial acetic acid. Sodium and boiling amyl alcohol reduce it to a tetrahydroretene, but if it heated with phosphorus and hydriodic acid to 260 °C, a dodecahydride is formed. Chromic acid oxidizes it to retene quinone, phthalic acid and acetic acid. It forms a picrate that melts at 123-124 °C.
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Names | |
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Preferred IUPAC name
1-Methyl-7-(propan-2-yl)phenanthrene | |
Other names
Retene | |
Identifiers | |
3D model (JSmol) |
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ChemSpider | |
ECHA InfoCard | 100.006.908 |
EC Number |
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PubChem CID |
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UNII | |
CompTox Dashboard (EPA) |
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Properties | |
C18H18 | |
Molar mass | 234.33552 |
Melting point | 98.5 °C (209.3 °F; 371.6 K) |
Boiling point | 390 °C (734 °F; 663 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Retene is derived by degradation of specific diterpenoids biologically produced by conifer trees. The presence of traces of retene in the air is an indicator of forest fires; it is a major product of pyrolysis of conifer trees.[1][failed verification – see discussion] It is also present in effluents from wood pulp and paper mills.[2]
Retene, together with cadalene, simonellite and ip-iHMN, is a biomarker of vascular plants, which makes it useful for paleobotanic analysis of rock sediments. The ratio of retene/cadalene in sediments can reveal the ratio of the genus Pinaceae in the biosphere.[3]
Health effects
A recent study has shown retene, which is a component of the Amazonian organic PM10, is cytotoxic to human lung cells.[4]
References
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